CA1335673C - Process for producing singly or multiply substituted organyl oxysilyl-functional thioureas and said compounds - Google Patents
Process for producing singly or multiply substituted organyl oxysilyl-functional thioureas and said compoundsInfo
- Publication number
- CA1335673C CA1335673C CA000603784A CA603784A CA1335673C CA 1335673 C CA1335673 C CA 1335673C CA 000603784 A CA000603784 A CA 000603784A CA 603784 A CA603784 A CA 603784A CA 1335673 C CA1335673 C CA 1335673C
- Authority
- CA
- Canada
- Prior art keywords
- c2h5o
- thioureas
- atoms
- amine
- oxysilyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003585 thioureas Chemical class 0.000 title claims abstract description 13
- 125000001190 organyl group Chemical group 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 14
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract description 10
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 6
- -1 aminoalkyl silane Chemical compound 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 150000003335 secondary amines Chemical class 0.000 abstract description 3
- ZPZDIFSPRVHGIF-UHFFFAOYSA-N 3-aminopropylsilicon Chemical compound NCCC[Si] ZPZDIFSPRVHGIF-UHFFFAOYSA-N 0.000 abstract description 2
- 150000004756 silanes Chemical class 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000000875 corresponding effect Effects 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 108020001305 NR1 subfamily Proteins 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000004659 dithiocarbamates Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 2
- DCYNAHFAQKMWDW-UHFFFAOYSA-N azane;carbamodithioic acid Chemical class N.NC(S)=S DCYNAHFAQKMWDW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 101150009274 nhr-1 gene Proteins 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GWQWBFBJCRDINE-UHFFFAOYSA-M sodium;carbamodithioate Chemical compound [Na+].NC([S-])=S GWQWBFBJCRDINE-UHFFFAOYSA-M 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical compound NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KUBPFQNPLTWBHU-UHFFFAOYSA-N 3-silylpropyl carbamodithioate Chemical compound C(N)(SCCC[SiH3])=S KUBPFQNPLTWBHU-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- DBAOJMMXPQSAKW-UHFFFAOYSA-M sodium;n-(3-triethoxysilylpropyl)carbamodithioate Chemical compound [Na+].CCO[Si](OCC)(OCC)CCCNC([S-])=S DBAOJMMXPQSAKW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3821465.2 | 1988-06-25 | ||
| DE3821465A DE3821465A1 (de) | 1988-06-25 | 1988-06-25 | Verfahren zur herstellung ein- oder mehrfach substituierter organyloxysilylfunktioneller thioharnstoffe und diese verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1335673C true CA1335673C (en) | 1995-05-23 |
Family
ID=6357229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000603784A Expired - Fee Related CA1335673C (en) | 1988-06-25 | 1989-06-23 | Process for producing singly or multiply substituted organyl oxysilyl-functional thioureas and said compounds |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0348620B1 (de) |
| JP (1) | JP2746663B2 (de) |
| AT (1) | ATE110731T1 (de) |
| CA (1) | CA1335673C (de) |
| DE (2) | DE3821465A1 (de) |
| ES (1) | ES2059604T3 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108218910A (zh) * | 2017-12-29 | 2018-06-29 | 烟台市裕盛化工有限公司 | 一类含硫脲结构的硅烷及其制备方法 |
| US10913805B2 (en) | 2017-07-31 | 2021-02-09 | Lg Chem, Ltd. | Modifier, method for preparing the same, and modified conjugated diene-based polymer including the same |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3925356A1 (de) * | 1989-07-31 | 1991-02-07 | Degussa | N,n'-disubstituierte und n,n,n'-/n,n',n'-trisubstituierte thioharnstoffe und verfahren zur herstellung (ii) |
| CA2311671A1 (en) * | 1999-08-13 | 2001-02-13 | Thierry Florent Materne | Nitrogen containing siloxy compounds |
| DE10053545A1 (de) | 2000-10-27 | 2002-05-08 | Henkel Kgaa | Polymere mit Harnstoffgruppen und Silylgruppen, deren Herstellung und Verwendung |
| US7074491B2 (en) * | 2003-11-04 | 2006-07-11 | Dionex Corporation | Polar silanes for binding to substrates and use of the bound substrates |
| JP2012240922A (ja) * | 2011-05-16 | 2012-12-10 | Shin-Etsu Chemical Co Ltd | 有機ケイ素化合物及びその製造方法、ゴム用配合剤、ゴム組成物並びにタイヤ |
| AU2012258576C1 (en) | 2011-05-25 | 2017-09-21 | Cidra Corporate Services Inc. | Mineral separation using sized-, weight- or magnetic-based polymer bubbles or beads |
| US9731221B2 (en) | 2011-05-25 | 2017-08-15 | Cidra Corporate Services, Inc. | Apparatus having polymer surfaces having a siloxane functional group |
| GB201115823D0 (en) * | 2011-09-13 | 2011-10-26 | Novel Polymer Solutions Ltd | Mineral processing |
| JP6291442B2 (ja) * | 2015-03-12 | 2018-03-14 | 京セラ株式会社 | サーミスタセンサ注形用樹脂組成物およびサーミスタセンサ |
| JP7208109B2 (ja) * | 2019-06-05 | 2023-01-18 | 信越化学工業株式会社 | オルガノシラン、表面処理剤、コーティング組成物および被膜物品 |
| CN116715694A (zh) * | 2023-04-23 | 2023-09-08 | 山东大学 | 一类含有硫脲键的硅烷偶联剂及其制备方法与在制备自修复硅橡胶中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2938046A (en) * | 1956-10-11 | 1960-05-24 | Union Carbide Corp | Dithiocarbamyl-containing silicon compounds |
| US3642855A (en) * | 1969-01-03 | 1972-02-15 | Gen Electric | Silyl-containing dithiocarbamates with functional groups on sulfuralkyl ester side chain |
| US3646089A (en) * | 1969-01-31 | 1972-02-29 | Gen Electric | Process for producing organosilicon compounds with isothiocyanate substituent bonded through divalent bridge |
| US4645846A (en) * | 1985-04-12 | 1987-02-24 | Scm Corporation | Silane compositions |
| DE3706521A1 (de) * | 1987-02-28 | 1988-09-08 | Degussa | Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung |
-
1988
- 1988-06-25 DE DE3821465A patent/DE3821465A1/de not_active Withdrawn
-
1989
- 1989-04-19 AT AT89106989T patent/ATE110731T1/de not_active IP Right Cessation
- 1989-04-19 ES ES89106989T patent/ES2059604T3/es not_active Expired - Lifetime
- 1989-04-19 DE DE58908261T patent/DE58908261D1/de not_active Expired - Fee Related
- 1989-04-19 EP EP89106989A patent/EP0348620B1/de not_active Expired - Lifetime
- 1989-06-23 CA CA000603784A patent/CA1335673C/en not_active Expired - Fee Related
- 1989-06-26 JP JP1161007A patent/JP2746663B2/ja not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10913805B2 (en) | 2017-07-31 | 2021-02-09 | Lg Chem, Ltd. | Modifier, method for preparing the same, and modified conjugated diene-based polymer including the same |
| CN108218910A (zh) * | 2017-12-29 | 2018-06-29 | 烟台市裕盛化工有限公司 | 一类含硫脲结构的硅烷及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE110731T1 (de) | 1994-09-15 |
| EP0348620B1 (de) | 1994-08-31 |
| JPH0245491A (ja) | 1990-02-15 |
| JP2746663B2 (ja) | 1998-05-06 |
| ES2059604T3 (es) | 1994-11-16 |
| DE3821465A1 (de) | 1989-12-28 |
| EP0348620A2 (de) | 1990-01-03 |
| EP0348620A3 (en) | 1990-11-07 |
| DE58908261D1 (de) | 1994-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1043346A (en) | Process for the production of sulphur-containing organosilicon compounds | |
| US5489701A (en) | Process for the preparation of silane polysulfides | |
| CA1335673C (en) | Process for producing singly or multiply substituted organyl oxysilyl-functional thioureas and said compounds | |
| US5596116A (en) | Process for the preparation of silane polysulfides | |
| US5466848A (en) | Process for the preparation of silane polysulfides | |
| US5684172A (en) | Process for the preparation of organosilicon polysulfide compounds | |
| US5684171A (en) | Process for the preparation of organosilicon polysulfide compounds | |
| US5675014A (en) | Process for the preparation of organosilicon disulfide compounds | |
| US5663358A (en) | Process for the preparation of organosilicon disulfide compounds | |
| KR100647445B1 (ko) | 고순도 유기규소디설판의 제조방법 | |
| GB1582412A (en) | Process for the production of sulphur-containing organosilicon compounds | |
| KR100834304B1 (ko) | 황 함유 유기규소 화합물의 제조방법 | |
| US6759545B2 (en) | Organosilicon compounds and preparation processes | |
| US4649208A (en) | Process for making amino group-containing organosilicon compounds | |
| US20110003989A1 (en) | Melamine-functional organosilicon compound and making method | |
| US5049690A (en) | N,N'-disubstituted and N,N,N'-/N,N', N'-trisubstituted thioureas and method of their preparation (II) | |
| WO2007068555A1 (de) | Verfahren zur herstellung von (mercaptoorganyl)alkylpolyethersilanen | |
| CA1336716C (en) | Process for producing substituted organyl oxysilyl-functional thioureas and said compounds | |
| US6218561B1 (en) | Process for the preparation of bis organosilicon disulfide compounds | |
| US4623741A (en) | Chlorosilane compounds | |
| EP1714968B1 (de) | Geschützte Piperazinogruppe enthaltende Organooxysilanverbindung und Herstellungsverfahren | |
| US5077420A (en) | Organosilicon compounds and method for their preparation | |
| KR102779692B1 (ko) | 질소 함유 환상 오르가녹시실란 화합물 및 그의 제조 방법 | |
| JP2005306783A (ja) | 黄色いスルフィド鎖含有有機ケイ素化合物の製造方法 | |
| MXPA98006336A (en) | Procedure for the preparation of organosilicio disulfans of alta pur |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |